Received 10 November 2012
The title compound, C17H19N3O2, crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules, the pyran ring has a twisted conformation (5S4), with Q = 0.301 (3) Å, = 116.7 (6) and = 213.6 (7)° for molecule A, and Q = 0.364 (2) Å, = 113.7 (3) and = 213.0 (4)° for molecule B. In molecule B, the terminal ethyl group is disordered over two orientations with an occupancy ratio of 0.55 (1):0.45 (1). In the crystal, molecules A and B form very similar but separate R12(7) motifs through N-HO and C-HO hydrogen bonds. The resulting chains along  are interlinked by weaker C-HO and C-H interactions, forming layers parallel to the bc plane.
For related structures, see: Rajalakshmi et al. (2012). For their biological activity, see: Kemnitzer et al. (2004); Mahdavi et al. (2011); Patil et al. (2012); Vosooghi et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLUTON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2085 ).
The authors thank the SAIF, IIT, Madras, India, for the X-ray intensity data collection facility.
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